Pathways Knowlegdes

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Pathway DOIs Note
phenylethanol biosynthesis

Accession ID: BioCyc:META_PWY-5751
  • 10.1016/j.phytochem.2007.06.005
  • 10.1073/pnas.0602469103
  • 10.1074/jbc.275.19.14659
  • 10.1074/jbc.m211914200
  • 10.1074/jbc.m602708200
  • 10.1271/bbb.70090
 Tieman DM, Loucas HM, Kim JY, Clark DG, Klee HJ. Tomato phenylacetaldehyde reductases catalyze the last step in the synthesis of the aroma volatile 2-phenylethanol. Phytochemistry. 2007 Nov;68(21):2660–9. doi: 10.1016/j.phytochem.2007.06.005. PMID: 17644147.; SAKAI M, HIRATA H, SAYAMA H, SEKIGUCHI K, ITANO H, ASAI T, DOHRA H, HARA M, WATANABE N. Production of 2-Phenylethanol in Roses as the Dominant Floral Scent Compound fromL-Phenylalanine by Two Key Enzymes, a PLP-Dependent Decarboxylase and a Phenylacetaldehyde Reductase. Bioscience, Biotechnology, and Biochemistry. 2007 Oct 23;71(10):2408–19. doi: 10.1271/bbb.70090.; Kaminaga Y, Schnepp J, Peel G, Kish CM, Ben-Nissan G, Weiss D, Orlova I, Lavie O, Rhodes D, Wood K, Porterfield DM, Cooper AJL, Schloss JV, Pichersky E, Vainstein A, Dudareva N. Plant Phenylacetaldehyde Synthase Is a Bifunctional Homotetrameric Enzyme That Catalyzes Phenylalanine Decarboxylation and Oxidation. Journal of Biological Chemistry. 2006 Aug;281(33):23357–66. doi: 10.1074/jbc.m602708200.; Tieman D, Taylor M, Schauer N, Fernie AR, Hanson AD, Klee HJ. Tomato aromatic amino acid decarboxylases participate in synthesis of the flavor volatiles 2-phenylethanol and 2-phenylacetaldehyde. Proc Natl Acad Sci U S A. 2006 May 23;103(21):8287–92. PMID: 16698923; PMCID: PMC1472464.; Dickinson JR, Salgado LEJ, Hewlins MJE. The Catabolism of Amino Acids to Long Chain and Complex Alcohols in Saccharomyces cerevisiae. Journal of Biological Chemistry. 2003 Mar;278(10):8028–34. doi: 10.1074/jbc.m211914200.; Wittstock U, Halkier BA. Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. Catalyzes the Conversion of l-Phenylalanine to Phenylacetaldoxime in the Biosynthesis of Benzylglucosinolate. Journal of Biological Chemistry. 2000 May;275(19):14659–66. doi: 10.1074/jbc.275.19.14659.
phenylethanol biosynthesis

Accession ID: BioCyc:CAULONA1000_PWY-5751		 -
tea aroma glycosidic precursor bioactivation

Accession ID: BioCyc:META_PWY-7114
  • 10.1016/0031-9422(93)85093-7
  • 10.1016/s0031-9422(00)00361-7
  • 10.1016/s1369-5266(02)00251-0
  • 10.1021/jf000443m
  • 10.1021/jf001077+
  • 10.1104/pp.102.011023
  • 10.1104/pp.121.2.325
  • 10.1271/bbb.58.1532
  • 10.1271/bbb.60.1815
  • 10.1271/bbb.60.929
  • 10.1271/bbb.65.2719
  • 10.1271/bbb.70447
 Saino H, Mizutani M, Hiratake J, Sakata K. Expression and biochemical characterization of beta-primeverosidase and application of beta-primeverosylamidine to affinity purification. Biosci Biotechnol Biochem. 2008 Feb;72(2):376–83. doi: 10.1271/bbb.70447. PMID: 18256510.; Mizutani M, Nakanishi H, Ema J, Ma SJ, Noguchi E, Inohara-Ochiai M, Fukuchi-Mizutani M, Nakao M, Sakata K. Cloning of beta-primeverosidase from tea leaves, a key enzyme in tea aroma formation. Plant Physiol. 2002 Dec;130(4):2164–76. PMID: 12481100; PMCID: PMC166728.; Pichersky E, Gershenzon J. The formation and function of plant volatiles: perfumes for pollinator attraction and defense. Curr Opin Plant Biol. 2002 Jun;5(3):237–43. doi: 10.1016/s1369-5266(02)00251-0. PMID: 11960742.; Ma SJ, Watanabe N, Yagi A, Sakata K. The (3R,9R)-3-hydroxy-7,8-dihydro-beta-ionol disaccharide glycoside is an aroma precursor in tea leaves. Phytochemistry. 2001 Apr;56(8):819–25. doi: 10.1016/s0031-9422(00)00361-7. PMID: 11324911.; Wang D, Kurasawa E, Yamaguchi Y, Kubota K, Kobayashi A. Analysis of glycosidically bound aroma precursors in tea leaves. 2. Changes in glycoside contents and glycosidase activities in tea leaves during the black tea manufacturing process. J Agric Food Chem. 2001 Apr;49(4):1900–3. doi: 10.1021/jf001077+. PMID: 11308343.; Ma SJ, Mizutani M, Hiratake J, Hayashi K, Yagi K, Watanabe N, Sakata K. Substrate specificity of beta-primeverosidase, a key enzyme in aroma formation during oolong tea and black tea manufacturing. Biosci Biotechnol Biochem. 2001 Dec;65(12):2719–29. doi: 10.1271/bbb.65.2719. PMID: 11826969.; Wang D, Yoshimura T, Kubota K, Kobayashi A. Analysis of glycosidically bound aroma precursors in tea leaves. 1. Qualitative and quantitative analyses of glycosides with aglycons as aroma compounds. J Agric Food Chem. 2000 Nov;48(11):5411–8. doi: 10.1021/jf000443m. PMID: 11087494.; Pare, Tumlinson. Plant volatiles as a defense against insect herbivores. Plant Physiol. 1999 Oct;121(2):325–32. PMID: 10517823; PMCID: PMC1539229.; Pattnaik S, Subramanyam VR, Bapaji M, Kole CR. Antibacterial and antifungal activity of aromatic constituents of essential oils. Microbios. 1997;89(358):39–46. PMID: 9218354.; Moon J, Watanabe N, Ijima Y, Yagi A, Sakata K. cis- andtrans-Linalool 3,7-Oxides and Methyl Salicylate Glycosides and (Z)-3-Hexenylß-D-Glucopyranoside as Aroma Precursors from Tea Leaves for Oolong Tea. Bioscience, Biotechnology, and Biochemistry. 1996 Jan;60(11):1815–9. doi: 10.1271/bbb.60.1815.; Nishikitani M, Kubota K, Kobayashi A, Sugawara F. Geranyl 6-O-a-L-Arabinopyranosyl-ß-D-glucopyranoside Isolated as an Aroma Precursor from Leaves of a Green Tea Cultivar. Bioscience, Biotechnology, and Biochemistry. 1996 Jan;60(5):929–31. doi: 10.1271/bbb.60.929.; Guo W, Hosoi R, Sakata K, Watanabe N, Yagi A, Ina K, Luo S. (S)-Linalyl, 2-Phenylethyl, and Benzyl Disaccharide Glycosides Isolated as Aroma Precursors from Oolong Tea Leaves. Bioscience, Biotechnology, and Biochemistry. 1994 Jan;58(8):1532–4. doi: 10.1271/bbb.58.1532.; Guo W, Sakata K, Watanabe N, Nakajima R, Yagi A, Ina K, Luo S. Geranyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside isolated as an aroma precursor from tea leaves for oolong tea. Phytochemistry. 1993 Aug;33(6):1373–5. doi: 10.1016/0031-9422(93)85093-7. PMID: 7763947.
L-phenylalanine degradation III

Accession ID: BioCyc:META_PWY-5079
  • 10.1074/jbc.m211914200
  • 10.1128/aem.69.8.4534-4541.2003
 Vuralhan Z, Morais MA, Tai S, Piper MDW, Pronk JT. Identification and Characterization of Phenylpyruvate Decarboxylase Genes in Saccharomyces cerevisiae. Appl Environ Microbiol. 2003 Aug;69(8):4534–41. doi: 10.1128/aem.69.8.4534-4541.2003.; Dickinson JR, Salgado LEJ, Hewlins MJE. The Catabolism of Amino Acids to Long Chain and Complex Alcohols in Saccharomyces cerevisiae. Journal of Biological Chemistry. 2003 Mar;278(10):8028–34. doi: 10.1074/jbc.m211914200.
phenylalanine degradation III

Accession ID: BioCyc:PLASMO_PWY-5079		 -
phenylalanine degradation III

Accession ID: BioCyc:PCHR_PWY-5079		 -
phenylethyl acetate biosynthesis

Accession ID: BioCyc:META_PWY-7075
  • 10.1002/yea.1382
  • 10.1007/s11103-005-4924-x
  • 10.1016/0003-9861(53)90063-0
  • 10.1104/pp.102.018572
  • 10.1104/pp.104.049981
  • 10.1146/annurev.arplant.56.032604.144128
 Lilly M, Bauer FF, Lambrechts MG, Swiegers JH, Cozzolino D, Pretorius IS. The effect of increased yeast alcohol acetyltransferase and esterase activity on the flavour profiles of wine and distillates. Yeast. 2006 Jul 15;23(9):641–59. doi: 10.1002/yea.1382. PMID: 16845703.; Guterman I, Masci T, Chen X, Negre F, Pichersky E, Dudareva N, Weiss D, Vainstein A. Generation of phenylpropanoid pathway-derived volatiles in transgenic plants: rose alcohol acetyltransferase produces phenylethyl acetate and benzyl acetate in petunia flowers. Plant Mol Biol. 2006 Mar;60(4):555–63. doi: 10.1007/s11103-005-4924-x. PMID: 16525891.; Gang DR. Evolution of flavors and scents. Annu Rev Plant Biol. 2005;56():301–25. doi: 10.1146/annurev.arplant.56.032604.144128. PMID: 15862098.; Dudareva N, Pichersky E, Gershenzon J. Biochemistry of plant volatiles. Plant Physiol. 2004 Aug;135(4):1893–902. PMID: 15326281; PMCID: PMC520761.; Shalit M, Guterman I, Volpin H, Bar E, Tamari T, Menda N, Adam Z, Zamir D, Vainstein A, Weiss D, Pichersky E, Lewinsohn E. Volatile ester formation in roses. Identification of an acetyl-coenzyme A. Geraniol/Citronellol acetyltransferase in developing rose petals. Plant Physiol. 2003 Apr;131(4):1868–76. PMID: 12692346; PMCID: PMC166943.; Gawron O, Grelecki CJ, Duggan M. The effect of substituents on the hydrolysis of phenyl acetate by wheat germ lipase. Archives of Biochemistry and Biophysics. 1953 Jun;44(2):455–67. doi: 10.1016/0003-9861(53)90063-0.
phenylethanol glycoconjugate biosynthesis

Accession ID: BioCyc:META_PWY-7074
  • 10.1007/s00425-007-0582-3
  • 10.1271/bbb.66.943
  • 10.1271/bbb.70404
 SAKAI M, TOMITA S, HIRATA H, ASAI T, DOHRA H, HARA M, WATANABE N. Purification and Characterization of ß-Glucosidase Involved in the Emission of 2-Phenylethanol from Rose Flowers. Bioscience, Biotechnology, and Biochemistry. 2008 Jan 23;72(1):219–21. doi: 10.1271/bbb.70404.; Hendel-Rahmanim K, Masci T, Vainstein A, Weiss D. Diurnal regulation of scent emission in rose flowers. Planta. 2007 Nov;226(6):1491–9. doi: 10.1007/s00425-007-0582-3. PMID: 17636322.; Watanabe S, Hayashi K, Yagi K, Asai T, MacTavish H, Picone J, Turnbull C, Watanabe N. Biogenesis of 2-phenylethanol in rose flowers: incorporation of [2H8]L-phenylalanine into 2-phenylethanol and its beta-D-glucopyranoside during the flower opening of Rosa 'Hoh-Jun' and Rosa damascena Mill. Biosci Biotechnol Biochem. 2002 May;66(5):943–7. doi: 10.1271/bbb.66.943. PMID: 12092844.
phenylalanine degradation

Accession ID: BioCyc:YEAST_PWY-5079		 -
phenylethanol biosynthesis

Accession ID: BioCyc:SMAN_PWY-5751		 -
phenylethanol biosynthesis

Accession ID: BioCyc:10403S_RAST_PWY-5751		 -
phenylalanine degradation III

Accession ID: BioCyc:THAPS_PWY-5079		 -
phenylalanine degradation

Accession ID: BioCyc:CALBI_PWY-5079
  • 10.1099/00221287-139-11-2783
 Derrick S, Large PJ. Activities of the enzymes of the Ehrlich pathway and formation of branched-chain alcohols in Saccharomyces cerevisiae and Candida utilis grown in continuous culture on valine or ammonium as sole nitrogen source. Journal of General Microbiology. 1993 Nov 01;139(11):2783–92. doi: 10.1099/00221287-139-11-2783.
L-phenylalanine degradation III

Accession ID: BioCyc:ARA_PWY-5079
  • 10.1093/jxb/erp390
  • 10.1104/pp.126.4.1678
 Gonda I, Bar E, Portnoy V, Lev S, Burger J, Schaffer AA, Tadmor Y, Gepstein S, Giovannoni JJ, Katzir N, Lewinsohn E. Branched-chain and aromatic amino acid catabolism into aroma volatiles in Cucumis melo L. fruit. J Exp Bot. 2010 Feb;61(4):1111–23. PMID: 20065117; PMCID: PMC2826658.; Lopukhina A, Dettenberg M, Weiler EW, Holländer-Czytko H. Cloning and characterization of a coronatine-regulated tyrosine aminotransferase from Arabidopsis. Plant Physiol. 2001 Aug;126(4):1678–87. PMID: 11500565; PMCID: PMC117166.
phenylalanine degradation III

Accession ID: BioCyc:MOUSE_PWY-5079		 -
phenylethanol biosynthesis

Accession ID: BioCyc:FLY_PWY-5751		 -
phenylethanol biosynthesis

Accession ID: BioCyc:THAPS_PWY-5751		 -
Metabolism and regulation

Accession ID: Plant Reactome:R-OAU-2744345		 -
Amino acid metabolism

Accession ID: Plant Reactome:R-OAU-2744343		 -
Ehrlich pathway

Accession ID: Plant Reactome:R-CME-1119267
  • 10.1016/j.molp.2015.09.005
  • 10.1105/tpc.110.078824
 Hildebrandt TM, Nunes Nesi A, Araújo WL, Braun HP. Amino Acid Catabolism in Plants. Mol Plant. 2015 Nov 02;8(11):1563–79. doi: 10.1016/j.molp.2015.09.005. PMID: 26384576.; Pribat A, Noiriel A, Morse AM, Davis JM, Fouquet R, Loizeau K, Ravanel S, Frank W, Haas R, Reski R, Bedair M, Sumner LW, Hanson AD. Nonflowering plants possess a unique folate-dependent phenylalanine hydroxylase that is localized in chloroplasts. Plant Cell. 2010 Oct;22(10):3410–22. PMID: 20959559; PMCID: PMC2990131.